Movies like
Loved the vibe? Here are ten films that hit similar notes—with match scores, reasons to watch, and where to stream in the US.
Chicago works as a comedy movie with a point of view—fans quote moments, but they also argue about what the film is actually saying about power, desire, or survival. The comedy and crime blend is the engine: it lets the film shift registers without feeling like two different movies stitched together.
Runtime 1h 53m · ★ 7.1
Mood
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Showing 10 of 10 picks
★ 8.0 · Comedy · Crime · Drama · 2h 9m
Why you'll love it
Fans of Chicago who respond to its comedy will find The Sting (1973) immediately familiar. Both films share a crime sensibility without ever feeling like carbon copies of each other.
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★ 7.7 · Music · Comedy · Action · 2h 13m
Why you'll love it
There's a reason Chicago fans keep landing on The Blues Brothers (1980) — the comedy is unmistakably related even when the plots diverge. Both films operate on the same emotional frequency, especially in their third acts.
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★ 8.1 · Comedy · Romance · Crime · 2h 3m
Why you'll love it
Some Like It Hot draws from the same comedy well as Chicago, channeling crime in ways that feel unmistakably related. The 1959 film makes a natural companion watch — similar in spirit but distinctly its own.
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★ 7.7 · Crime · Drama · Mystery · 2h 10m
Why you'll love it
Primal Fear (1996) captures the crime appeal of Chicago without simply imitating it. The drama streak running through both films is what puts Primal Fear at the top of any "if you liked…" shortlist.
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★ 7.2 · Drama · Thriller · Crime · 1h 36m
Why you'll love it
The crime appeal of Chicago — that dark edge, the drama — translates cleanly into A History of Violence (2005). Different setting, same essential satisfaction.
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★ 7.1 · Drama · Comedy · Romance · 1h 53m
Why you'll love it
The filmmakers behind High Fidelity (2000) clearly understood what makes comedy work — the same quality that keeps Chicago rewatchable. Expect the same funny rhythm, executed with a fresh angle.
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★ 6.7 · Crime · Action · Comedy · 1h 36m
Why you'll love it
48 Hrs. (1982) is the kind of film Chicago fans discover and immediately send to their group chat. The comedy overlap is real, but it's the funny emotional pull that seals the recommendation.
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★ 6.6 · Romance · Comedy · Drama · 1h 38m
Why you'll love it
Risky Business shares Chicago's gift for comedy — the 1983 film delivers drama without overstaying its welcome. Consider it required viewing once you've finished rewatching your first pick.
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★ 7.1 · Crime · Drama · Thriller · 1h 45m
Why you'll love it
Much of what makes Chicago compelling — the crime, the drama — shows up in The Outfit (2022) in a slightly different form. Both films understand that dark storytelling works best when it trusts the audience.
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★ 6.9 · Comedy · Drama · 1h 56m
Why you'll love it
The comedy energy of Chicago is alive in The War of the Roses (1989), filtered through a different story but the same emotional register. It earns its place on this list with a funny payoff that rivals the original pick.
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